Around 0330 hrs (timezone -7.5) on 15 December 1941 HrMs O 16 (Lt. 1e Klasse (Lt.Cdr.) Antoine Jacobus Bussemaker, RNN) hit a mine off Tioman island in postion 03º10'N, 104º19'E. 41 men were lost which includes the Commanding officer. There was only one survivor who reached and Island after being in the water for about 35 hours.

As O 16 did not return from patrol and there is no official patrol report it is not known when she reached her patrol position.

According to the sole survivor of O 16 she attacked a Japanese transport ship with three torpedoes (maybe in more than one attack) during the night of 10 / 11 December 1941.

12 Dec 1941In the evening of 12 December 1941, now off Patani, Siam, HrMs O 16 (Lt.Cdr. A.J. Bussemaker, RNN) torpedoed and sank three Japanese transport ships, Tosan Maru (8666 GRT, built 1938), Kinka Maru (9305 GRT, built 1938) and Asosan Maru (8812 GRT, built 1934). These ships were sunk in shallow water and were later raised and repaired. After these attacks O 16 set course towards Singapore.